Born in 1947 in Montgomery, Alabama, Democrat Dorothy Tillman is a former alderman (City Council member) of Chicago’s largely black Third Ward. Well known for her collection of garish, broad-brimmed hats and her unpredictable behavior -- she once brandished a handgun at a City Council meeting -- Tillman is also infamous for her revealed record of municipal corruption, her uncompromising views on race, and her professed anti-Americanism. Moreover, she is a longtime friend of Barack Obama.

At the age of 16 in her native Alabama, Tillman began working as an organizer with Martin Luther King, Jr.'s Southern Christian Leadership Conference (SCLC). When King decided to shift his operations from the South to Chicago in 1965, Tillman was sent to the city to lay the groundwork for his arrival.

She struggled with this charge. The black and white moral situation in the segregated South, which made organizing relatively easy (if physically dangerous) there, dissolved into gray ambiguity in the North, where racism was more subtle and where a local black power structure was invested in the status quo. The confrontational style of Southern activists like Tillman ill-suited Chicago’s black residents, and the reception she received was not a warm one. "[W]e could not find a church pastored by a black minister … that would give the SCLC office space," Tillman would later complain. "Therefore, we ended up with a white pastor.” Outraged, Tillman dismissed Chicago’s blacks as “Uncle Toms.”

In Tillman's judgment, Chicago’s machine politics had made blacks dependent on the patronage of the city’s white Democratic establishment. So debilitating was this dependence, Tillman charged, that “[b]lacks in this city were worse off than any plantation down South.” What was needed, she said, was a politics of black empowerment that would build up an independent black political machine to counter the dominant white one that had co-opted black leadership since the turn of the century.

Tillman would get her chance to pursue this vision in 1984, when elected alderman Tyrone Kenner was forced out of the City Council after being convicted for extortion (he had been collecting commissions for “selling” city jobs). Then-mayor Harold Washington tapped Tillman to fill the vacancy. Despite initial resistance -- one alderman reportedly refused to support the appointment because Tillman had called him an obscene name -- she won the backing of the Council and the voters.

Tillman quickly amassed great political clout in Chicago. In 1987 she carried the Third Ward with nearly 80 percent of the vote. She would remain a political fixture in the City Council until 2006.

During her time in elected politics, Tillman became the leading -- and arguably most acerbic -- proponent of reparations for slavery. In 2001, for instance, she hosted the first ever “National Reparations Convention for African-American Descendants of African Slaves” in Chicago. Under Tillman’s direction, the convention drafted a “national plan” that would have compelled the federal government and American corporations to provide reparations to the descendants of American slaves.

Slavery, Tillman insisted, had “put the freed slaves and their descendants at a disadvantage that will never be overcome without reparations.” Claiming that America remains “one of the cruelest nations in the world when it comes to black folks,” Tillman declares that the U.S. “owes blacks a debt.”

At a 2001 political reception held at Chicago's posh Palmer House Hilton hotel, Tillman touched off a citywide scandal when she demanded that she be served by only black waiters. Two white waiters later brought suit against Tillman, charging that she had caused them to be removed from the reception unjustifiably. In the aftermath of the scandal, the alderwoman explained: "It is not personal against anybody. I am just pro-my people. Being pro-black is not being pro-racist.”

In 2004 Tillman was among the politicians whose backing of Barack Obama’s U.S. Senate run helped the latter win Chicago’s predominantly black wards, where Obama captured more than 90 percent of the vote against his heavily favored opponent, multimillionaire businessman Blair Hull.

In 2005 Tillman was an honored guest at a lecture by Louis Farrakhan, whom she praised as a patron of the community. “We have always supported the minister when others were running away,” said Tillman. “I am thankful for the role for the role that we played.”

Throughout her political career, Tillman’s critics charged that she had abused her authority as alderwoman in order to secure city funds for development projects. While community groups had their requests denied, Tillman seemed always to have her hands on the city’s purse strings.

Allegations of this sort came to a head in 2006. A local newspaper, Lakefront Outlook, launched an investigation into Tillman’s financial books and discovered a pattern of suspicious financial irregularities stemming from her pet project, a taxpayer-funded facility called the Harold Washington Center. According to the paper’s findings, the Center, built directly across the street from Tillman’s office, was marred by tax violations. The investigators found further that Tillman was engaging in blatant nepotism, hiring family members to staff the financially troubled institution. One of Tillman’s daughters, for example, ran both the Center and the catering service that supplied it.

On the strength of these and other revelations, Tillman’s challenger (for her alderman post) Pat Dowell, a former deputy executive in Chicago’s Department of Planning and Development, was able to paint Tillman as being “out of touch with the people in the community.” With her penchant for playing the race card -- Tillman had long adopted the tactic of assailing the mere presence of political opposition as evidence of “racism” -- rendered ineffective against her black opponent, Tillman was voted out of office.

Tillman’s loss came despite the support of most the city’s black community. Her most prominent backer was then-U.S. Senator Barack Obama. Explaining that Tillman had been “a very early supporter of my [Senate] campaign,” Obama endorsed Tillman in the Third Ward race.

This profile is adapted from the article "Obama's World, Part II," authored by Jacob Laksin and published by FrontPageMag.com on May 8, 2008.